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sapropterin (CHEBI:59560)

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ChEBI Name sapropterin
ChEBI ID CHEBI:59560
Definition A tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6R,1'R,2'S-enantiomer).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Secondary ChEBI IDs CHEBI:64242
Supplier Information
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Formula Source
C9H15N5O3 ChEBI
Net Charge 0
Average Mass 241.24710
InChI
InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
InChIKey
FNKQXYHWGSIFBK-RPDRRWSUSA-N
SMILES
[H][C@@]1(CNc2nc(N)[nH]c(=O)c2N1)[C@@H](O)[C@H](C)O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
(via 5,6,7,8-tetrahydrobiopterin )
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
(via 5,6,7,8-tetrahydrobiopterin )
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via 5,6,7,8-tetrahydrobiopterin )
Application(s): diagnostic agent
A substance administered to aid diagnosis of a disease.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via 5,6,7,8-tetrahydrobiopterin )
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing sapropterin (CHEBI:59560) has role coenzyme (CHEBI:23354)
sapropterin (CHEBI:59560) has role diagnostic agent (CHEBI:33295)
sapropterin (CHEBI:59560) has role metabolite (CHEBI:25212)
sapropterin (CHEBI:59560) is a 5,6,7,8-tetrahydrobiopterin (CHEBI:15372)
Incoming sapropterin dihydrochloride (CHEBI:32120) has part sapropterin (CHEBI:59560)
IUPAC Name
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(3H)-one
INNs Sources
sapropterin ChemIDplus
sapropterina ChemIDplus
sapropterinum ChemIDplus
Synonyms Sources
(−)-(6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone ChemIDplus
(6R)-L-erythro-tetrahydrobiopterin ChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone KEGG COMPOUND
5,6,7,8-Tetrahydrobiopterin KEGG COMPOUND
6R-5,6,7,8-tetrahydrobiopterin ChemIDplus
6R-BH4 ChEBI
6R-L-5,6,7,8-tetrahydrobiopterin ChemIDplus
L-erythro-tetrahydrobiopterin UniProt
R-THBP ChEBI
tetrahydrobiopterin DrugBank
Database Links Databases
C00018229 KNApSAcK
C00272 KEGG COMPOUND
CPD-14053 MetaCyc
D08505 KEGG DRUG
DB00360 DrugBank
EP191335 Patent
H4B PDBeChem
HMDB00787 HMDB
Sapropterin Wikipedia
US4713454 Patent
View more database links
Registry Numbers Types Sources
17528-72-2 CAS Registry Number KEGG COMPOUND
27070-47-9 CAS Registry Number ChemIDplus
4699705 Reaxys Registry Number Reaxys
4699705 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10333495 PubMed citation SUBMITTER
1297822 PubMed citation CiteXplore
16510994 PubMed citation SUBMITTER
19627172 PubMed citation CiteXplore
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23712020 PubMed citation CiteXplore
23743404 PubMed citation CiteXplore
4004257 PubMed citation CiteXplore
General Comment
2011-03-17 The active enantiomer of tetrahydrobiopterin, sapropterin is a natural co-factor of the three aromatic amino acid hydroxylase enzymes responsible for the conversion of phenylalanine to tyrosine, tyrosine to L-dopa, and tryptophan to 5-hydroxytryptophan. These conversions are particularly important in the biosynthesis of the neurotransmitters serotonin, melatonin, dopamine, noradrenaline and adrenaline. Sapropterin is also an essential cofactor in the biosynthesis of nitric oxide. It is used as its dihydrochloride for the diagnosis and treatment of variant forms of phenylketonuria (hyperphenylalaninaemia) associated with tetrahydrobiopterin deficiency.
 
Last Modified
28 July 2014

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